2-phenyl-4-(3,4,5-trimethoxyphenyl)quinoline | 1447235-58-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-phenyl-4-(3,4,5-trimethoxyphenyl)quinoline
• 英文别名: 2-Phenyl-4-(3,4,5-trimethoxyphenyl)quinoline
• CAS: 1447235-58-6
• 化学式: C₂₄H₂₁NO₃
• 分子量: 371.436
• InChiKey: FURORQPBUPMBMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-4-methyl-N-((E)-1-phenyl-3-(3,4,5-trimethoxyphenyl)allylidene)benzenesulfonamide 在 sodium hydroxide 、 亚硝酸异戊酯 、 三氯乙酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 2-phenyl-4-(3,4,5-trimethoxyphenyl)quinoline
  参考文献：
  名称：

  Synthesis of Quinolines from N-Tosyl-1-azadienes

  摘要：

  A route to aryl-substituted quinolines from N-tosyl 1-azadienes is described. The key steps are a [4+2] cycloaddition with benzyne followed by base treatment of the 1,4-dihydroquinoline product. The N-tosyl 1-azadienes were prepared from readily accessible cinnamaldehyde and chalcone substrates by condensation with p-TsNH2. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.726388

文献信息

• Gold(I)-Catalyzed [4 + 2] Annulation between Arylynes and C,N-Diaryl Nitrones for Chemoselective Synthesis of Quinoline Scaffolds via Gold Acetylide Intermediates
  作者：Debashis Barik、Rai-Shung Liu

  DOI：10.1021/acs.joc.2c00274

  日期：2022.6.3

  Gold-catalyzed synthesis of quinoline derivatives via [4 + 2] annulation between terminal arylynes and nitrones is described. Our mechanistic analysis supports the participation of alkynylgold intermediates, instead of a typical gold–carbene species in recently reported gold catalysis. These nucleophilic alkynylgold species react with nitrones via Povarov-type reactions. Cheap, readily available materials

  描述了通过末端芳炔和硝酮之间的 [4 + 2] 环化合成喹啉衍生物的金催化合成。我们的机理分析支持炔基金中间体的参与，而不是最近报道的金催化中的典型金-卡宾物质。这些亲核炔基金物质通过波瓦罗夫型反应与硝酮反应。廉价、容易获得的材料和广泛的基材范围体现了这种方法的优势。
• Synthesis of Quinolines from <i>N</i>-Tosyl-1-azadienes
  作者：Sean Stokes、Keith T. Mead

  DOI：10.1080/00397911.2012.726388

  日期：2013.10.2

  A route to aryl-substituted quinolines from N-tosyl 1-azadienes is described. The key steps are a [4+2] cycloaddition with benzyne followed by base treatment of the 1,4-dihydroquinoline product. The N-tosyl 1-azadienes were prepared from readily accessible cinnamaldehyde and chalcone substrates by condensation with p-TsNH2. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.